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Merck
CN

188174

(+)-4-Cholesten-3-one

98%

Synonym(s):

3-Keto-4-cholestene, 3-Oxo-4-cholestene, 4-Cholesten-3-one

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
601-57-0
Molecular Weight:
384.64
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
24851303
EC Number:
210-005-1
Beilstein/REAXYS Number:
2224119
MDL number:
MFCD00003663
Assay:
98%
Form:
solid

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InChI key

NYOXRYYXRWJDKP-GYKMGIIDSA-N

InChI

1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

SMILES string

[H][C@@]12[C@]([C@](CC3)(C)C(CC2)=CC3=O)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCCC(C)C

assay

98%

form

solid

optical activity

[α]23/D +91.0°, c = 2 in chloroform

mp

79-81 °C (lit.)

functional group

ketone

Quality Level

100

Related Categories

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8231
STBH6865
STBF4322V
STBC4769V
10120TH

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Daniel L Motola et al.
Cell, 124(6), 1209-1223 (2006-03-15)
In response to environmental and dietary cues, the C. elegans orphan nuclear receptor, DAF-12, regulates dauer diapause, reproductive development, fat metabolism, and life span. Despite strong evidence for hormonal control, the identification of the DAF-12 ligand has remained elusive. In
B Zipser et al.
Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology, 120(2), 269-282 (1998-11-25)
Steroids were isolated from the blood-sucking leech species Hirudo medicinalis and their structure was studied with one- and two-dimensional NMR spectroscopy (DQF-COSY and HMQC), GC-MS and ESI-MS spectrometry. Fractionating leech lipid using silicic acid chromatography led to the isolation of
Jenna K Capyk et al.
The Journal of biological chemistry, 284(51), 35534-35542 (2009-10-23)
Cyp125 (Rv3545c), a cytochrome P450, is encoded as part of the cholesterol degradation gene cluster conserved among members of the Mycobacterium tuberculosis complex. This enzyme has been implicated in mycobacterial pathogenesis, and a homologue initiates cholesterol catabolism in the soil
Hugues Ouellet et al.
Molecular microbiology, 77(3), 730-742 (2010-06-16)
The infectivity and persistence of Mycobacterium tuberculosis requires the utilization of host cell cholesterol. We have examined the specific role of cytochrome P450 CYP125A1 in the cholesterol degradation pathway using genetic, biochemical and high-resolution mass spectrometric approaches. The analysis of
Jonathan B Johnston et al.
The Journal of biological chemistry, 285(47), 36352-36360 (2010-09-17)
One challenge to the development of new antitubercular drugs is the existence of multiple virulent strains that differ genetically. We and others have recently demonstrated that CYP125A1 is a steroid C(26)-monooxygenase that plays a key role in cholesterol catabolism in
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